Benzylamine → 6-benzylamino-2-(4-tert-butoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

To toluene (40 ml) were added palladium(II) acetate (27 mg) and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (240 mg) at room temperature, and the mixture was stirred for 5 min. under a nitrogen stream. To the reaction mixture were added 6-bromo-2-(4-tert-butoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (2.0 g) and benzylamine (0.6 ml) at room temperature and the mixture was stirred for 10 min. under a nitrogen stream. Further, to the reaction mixture was added sodium tert-butoxide (480 mg) at room temperature and the mixture was heated under reflux under a nitrogen atmosphere for 12 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=1:1) to give the title compound (1.8 g).

1. stirringthe mixture was stirred for 10 min. under a nitrogen stream
2. temperaturethe mixture was heated
3. temperatureunder reflux under a nitrogen atmosphere for 12 hr
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with water and saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customthe obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=1:1)

ORD record

ord-6e06d062824946a5b86c5767b498f049

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402595B2